ethyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oate
• 英文别名: ethyl (1R,3aS,5aR,5bR,7aR,8R,11aR,11bR,13aR,13bR)-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• 化学式: C₃₂H₅₀O₄
• 分子量: 498.747
• InChiKey: HQQDOHUYJSWWLS-OVWXUPSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oate 在 吡啶 、 盐酸羟胺 作用下， 反应 4.0h， 以56.3%的产率得到ethyl 3-hydroxyimino-23-hydroxy-lup-20(29)-en-28-oate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives

  摘要：

  A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, 816 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50 values of 5.85, 6.23 and 7.22 mu M against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.058
• 作为产物：
  描述：

  23-hydroxybetulinic acid 在 盐酸 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 44.0h， 生成 ethyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives

  摘要：

  A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, 816 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50 values of 5.85, 6.23 and 7.22 mu M against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.058

文献信息

• Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives
  作者：Hengyuan Zhang、Peiqing Zhu、Jie Liu、Xue Yang、Shengtao Xu、Hequan Yao、Jieyun Jiang、Wencai Ye、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.ejmech.2014.09.058

  日期：2014.11

  A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, 816 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50 values of 5.85, 6.23 and 7.22 mu M against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.